A triclinic polymorph of N-[4-(4-methyl­benzene­sulfonamido)­phenyl­sulfon­yl]acetamide

Khizar Hayat; Muhammad Nadeem Asghar; M Nawaz Tahir; Muhammad Shafiq; Dildar Ahmad

doi:10.1107/S1600536812008616

. 2012 Mar 7;68(Pt 4):o983–o984. doi: 10.1107/S1600536812008616

A triclinic polymorph of N-[4-(4-methylbenzenesulfonamido)phenylsulfonyl]acetamide

Khizar Hayat ^a, Muhammad Nadeem Asghar ^a, M Nawaz Tahir ^b,^*, Muhammad Shafiq ^c, Dildar Ahmad ^a

PMCID: PMC3343954 PMID: 22590035

Abstract

In the asymmetric unit of the title compound, C₁₅H₁₆N₂O₅S₂, there are two symmetry-independent molecules which adopt similar conformations, with dihedral angles between the aromatic rings of 59.30 (8) and 61.81 (8)°, and dihedral angles between acetamide group and the benzene ring of 77.08 (10) and 78.40 (10)°. Each type of molecule forms similar one-dimensional polymeric structures extending along the b axis via N—H⋯O hydrogen bonds. These hydrogen bonds generate two types of centrosymmetric motifs, R ₂ ²(8) and R ₂ ²(20). Moreover C—H⋯O interactions assemble the molecules into a three-dimensional framework. The crystal structure was determined from a non-merohedral twin [ratio of the twin components = 0.322 (4):0.678 (4)].

Related literature

For a monoclinic polymorph of the title compound, see: Ashfaq et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₆N₂O₅S₂
M _r = 368.42
Triclinic,
a = 9.6722 (3) Å
b = 11.9968 (4) Å
c = 15.4784 (6) Å
α = 82.802 (2)°
β = 79.232 (1)°
γ = 89.653 (2)°
V = 1750.24 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.915, T _max = 0.938
31011 measured reflections
8382 independent reflections
5598 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.153
S = 1.02
8382 reflections
438 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008616/gk2456sup1.cif

e-68-0o983-sup1.cif^{(38.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008616/gk2456Isup2.hkl

e-68-0o983-Isup2.hkl^{(401.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008616/gk2456Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.86	2.14	2.841 (3)	138
N2—H2A⋯O4ⁱⁱ	0.86	2.06	2.876 (3)	158
N3—H3A⋯O10ⁱⁱⁱ	0.86	2.18	2.859 (3)	136
N4—H4⋯O8^iv	0.86	2.05	2.867 (3)	157
C13—H13⋯O2	0.93	2.49	3.062 (4)	120
C22—H22A⋯O6^v	0.96	2.59	3.338 (5)	135
C24—H24⋯O6	0.93	2.46	3.026 (4)	119

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as a part of the series of sulfonamide derivatives. The aim of our research work is to find the potential sulfonamide derivatives possesing anti-microbial activity. The crystal structure of the monoclinic polymorph of the title compound has been reported earlier by Ashfaq et al. (2010). The molecules in the two polymorphs differ in conformation.

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the toluene group A (C1–C7), benzene ring B (C8–C13) and the acetamide group C (N2/C14/C15/O5) are planar with r. m. s. deviation of 0.0089 Å, 0.0080 Å and 0.0028 Å, respectively. The dihedral angles between A/B, A/C and B/C are 61.81 (8)°, 45.90 (14)° and 77.08 (10)°, respectively. In second molecule, the toluene group D (C16–C22), benzene ring E (C23–C28) and the acetamide group F (N4/C29/C30/O10) are planar with r. m. s. deviation of 0.0116 Å, 0.0066 Å and 0.0006 Å, respectively. The dihedral angles between D/E, D/F and E/F are 59.30 (8)°, 46.10 (14)° and 78.40 (10)°, respectively. The dihedral angle between two aromatic rings in its polymrph (Ashfaq et al., 2010) is 81.33 (6)° compared to 61.81 (8)° and 59.30 (8)°. In both molecules, there exist weak intramolecular H–bonding of C—H···O type (Table 1). Both molecules are dimerized themselves due to intermolecular H-bonding of N—H···O type forming R₂²(8) ring motifs (Bernstein et al., 1995). The dimers are interliked due to strong N—H···O type of H–bondings (Table 1, Fig. 2) and form R₂²(20) ring motifs.

Experimental

Equal molar ratio of N-[(4-aminophenyl)sulfonyl]acetamide and p-toluene sulfonyl chloride was dissolved in 20 ml distilled water. The solution with pH = 8–9 adjusted using Na₂CO₃ (1 M) was stirrered at room temperature for 6 h. Progress of the reaction was monitored by the consumption of suspended p-toluene sulfonyl chloride. On completion, pH was adjusted to 2–3 using HCl (2 N). The precipitate formed was filtered, washed with ditilled water and recrystallized from methanol to afford colorless prisms with m.p. 385 K.